An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core

Alexander K. Eltyshev, Polina O. Suntsova, Ksenia D. Karmatskaia, Olga S. Taniya, Pavel A. Slepukhin, Enrico Benassi, Nataliya P. Belskaya

Research output: Contribution to journalArticle

Abstract

A convenient synthesis of 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones (DTPs) from 3,3-diamino-2-(arylazo)acrylonitriles through a versatile and readily accessible two-step procedure is described. Density functional theory (DFT) calculations were performed to explain the selectivity of the heterocyclization step, which predominantly afforded 6-amino-5-(arylazo)pyrimidin-2(1H)-thiones in chloroform or ethanol, and 2,3-dihydro-1,2,4-triazines in toluene or DMF. Novel 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones were obtained in good yields and showed absorption in the ultraviolet region and good emission in the blue region. The photophysical properties of DTPs were better than those cited in select literature examples of 8-azapurines. Owing to the facile synthesis and good photophysical characteristics in an aqueous medium, the new DTPs should have potential applications as organic fluorophores in fluorescence imaging and materials science.

Original languageEnglish
Pages (from-to)9420-9429
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number48
DOIs
Publication statusPublished - 1 Jan 2018
Externally publishedYes

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Acrylonitrile
Thiones
Fluorophores
Optical Imaging
Toluene
Chloroform
Ethanol
acrylonitriles
Materials science
synthesis
materials science
chloroform
Density functional theory
toluene
ethyl alcohol
selectivity
Fluorescence
density functional theory
Imaging techniques
fluorescence

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Eltyshev, A. K., Suntsova, P. O., Karmatskaia, K. D., Taniya, O. S., Slepukhin, P. A., Benassi, E., & Belskaya, N. P. (2018). An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core. Organic and Biomolecular Chemistry, 16(48), 9420-9429. https://doi.org/10.1039/c8ob02644k

An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core. / Eltyshev, Alexander K.; Suntsova, Polina O.; Karmatskaia, Ksenia D.; Taniya, Olga S.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 48, 01.01.2018, p. 9420-9429.

Research output: Contribution to journalArticle

Eltyshev, AK, Suntsova, PO, Karmatskaia, KD, Taniya, OS, Slepukhin, PA, Benassi, E & Belskaya, NP 2018, 'An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core', Organic and Biomolecular Chemistry, vol. 16, no. 48, pp. 9420-9429. https://doi.org/10.1039/c8ob02644k
Eltyshev, Alexander K. ; Suntsova, Polina O. ; Karmatskaia, Ksenia D. ; Taniya, Olga S. ; Slepukhin, Pavel A. ; Benassi, Enrico ; Belskaya, Nataliya P. / An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 48. pp. 9420-9429.
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